Ammonium Chloride → Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate

HRID 1067770ノート

反応式

HRID 1067770 の反応式
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([Cl:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([OH:21])(=[O:20])[CH3:19].C([N:24]=[N+:25]=[N-:26])C.[O-][CH2:28][CH3:29].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:19]([N:24]=[N+:25]=[N-:26])[C:18]([O:21][CH2:28][CH3:29])=[O:20])=[C:11]([Cl:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 140340774-(Benzyloxy)-2-chlorobenzaldehydeHCID 86756206HCID 86756206、化合物

生成物 1

HCID 53783165Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate収率 57.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
-10 °C

実験手順

An ethanol solution, 70 ml, containing 5.40 g (21.9 mmol) of 4-benzyloxy-2-chlorobenzaldehyde and 11.3 g (87.6 mmol) of ethyl azide acetate was gradually added dropwise to 70 ml of an ethanol solution of 5.95 g (87.6 mmol) of sodium ethoxide at −10° C. After stirring at −10° C. for further 5 hours, the reaction temperature was slowly elevated to room temperature. The reaction mixture was poured onto 200 ml of saturated ammonium chloride aqueous solution and the mixture was extracted three times with ethyl acetate. The combined extracts were then washed with saturated ammonium chloride solution and next with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4.50 g (57.5%) of ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate.

後処理

  1. customwas slowly elevated to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe combined extracts were then washed with saturated ammonium chloride solution and next with saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-6815f5fbd6a848b684179df6d26b0a48
出典データセット
uspto-grants-2001_06
特許番号
US06248772B1

反応ノート

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